Flying east
Hopkins (CLE) flies nonstop to all three D.C. airports. American Eagle goes to Reagan National, United to Dulles, Southwest to BWI.
Closer to Akron or Canton? Akron-Canton (CAK) has its own American Eagle nonstop to Reagan National.
Land at Reagan National and you can walk to a Metro stop, on the Blue and Yellow lines. Land at BWI and Amtrak or MARC takes you into Union Station.
Getting to Hopkins is easy. It was the first airport in the country tied straight into rail transit, and the RTA Red Line still runs from the terminal to Tower City.
Driving west
Neither Hopkins nor Akron-Canton flies nonstop to Milwaukee, so June is a road trip. It's a long day's drive west on I-90, past Toledo and around Chicago, and you gain an hour on the way.
Train, or the long drive east
Amtrak's lakefront station downtown has a daily train toward Washington, but it comes through in the middle of the night. By car, D.C. is about a day's drive east.
Hopkins also flies nonstop to Phoenix on American, Frontier and Southwest, if a Phoenix card up top fits your year better.